


Damned If I Do Ya (Damned If I Don't)

by TheNameIsZ (curiouslygray)



Category: The Flash (TV 2014)
Genre: Angel/Devil - Freeform, Deal with a Devil, Descriptions of Alcoholism, Enemies to Friends to Lovers, Guardian Angels, M/M, OC, Ship Swap, descriptions of abuse, probably out of character
Language: English
Status: Completed
Published: 2019-04-23
Updated: 2019-04-23
Packaged: 2020-01-24 08:12:45
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,939
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18567397
Author URL: https://archiveofourown.org/users/curiouslygray/pseuds/TheNameIsZ
Summary: Leonard is a Guardian Angel. The human he’s assigned to hasn’t had a good stroke of luck in years. When a devil shows up to make a deal with the human, Leonard determined to stop it.





	Damned If I Do Ya (Damned If I Don't)

**Author's Note:**

  * For [The_DoctorSimba](https://archiveofourown.org/users/The_DoctorSimba/gifts).



> Hey there everyone!  
> So, I normally write for SuperCorp and my friend (for who this is gifted) normally writes for ColdFlash. Back in February, we brought up the idea of doing a ship swap: I write for ColdFlash and they write for SuperCorp. About a month and a half later, we've finally fulfilled that idea. We both used the same prompt and wrote using only our previous knowledge. We've beta read for each other in past, as well as shared many snippets from various fan fics we've read, so we're vaguely familiar at the very least. Due to this, I do apologize for any "out of character"ness or lore bits that may just be wrong. I did try to double check more important things with my friend, but, well, sometimes you miss things.
> 
> Hope you all enjoy!
> 
> Prompt (from a tumblr post): I love contrasting designs… Demons wearing white clothes……….. Angels wearing black clothes…………………… A demon so beautiful they are mistaken for an angel; an angel so monstrous they are mistaken for a demon. (And then they kiss)
> 
> Title from All Time Low song of the same name.

Chris had been down on his luck for quite a few years now. He’d been a senior in college when his longtime girlfriend broke up with him, leaving him so distraught he almost had to go another semester. Post-graduation, he struggled finding a job in his field, eventually taking a job as a mail sorter to at least have some form of income. The dog he adopted helped, but he was still alone in Central City.

Leonard sighed as he watched him from the window seat. Chris was scrolling through job postings at the coffee shop just down the street from his apartment. Leonard hoped the man would find something to bolster his spirit. Until then, he’d just stay in the shadows, preventing him from walking in front of an oncoming car or steering him away from dark alleyways on his way home from work. Nothing out of the usual for a standard guardian angel.

When something dark pricked at his sense, Leonard wasn’t surprised. It was a big city; it could be any number of things. Corrupt politicians, criminals, a cryptid in hiding, perhaps a witch who was dabbling in something darker.

He was surprised, however, when he located the source. A few buildings down was lean man dressed in a crisp white suit with dark red accents. Leonard narrowed his eyes, carefully watching the man. He recognized his kind simply by his aura: a dealer.

Devils and demons walked the earth. Some came about through the horrors and atrocities committed by humans: war, murder, genocide, famine. Some were sent here to try to push humans towards certain choices, generally leading towards the aforementioned horrors. Some, like the devil who now stood outside the coffee shop door, were here simply to make deals. They weren’t the most powerful devils, but certainly some of the most prolific and dangerous.

Now that the devil had crossed the threshold into the coffee shop, walking through the door as if it wasn’t even there, Leonard could get a better look at him. He was clean shaven, hair short and slicked back, a cheeky, almost goofy grin as he rocked back on the heels of his shiny, scarlet loafers. The devil scanned the room, looking for his target, Leonard assumed. He crossed his arms, setting his jaw as he stared down the devil.

When the devil’s green eyes landed on the angel, Leonard could have sworn they sparkled with mischief. The devil gave him a mock bow, tipping an invisible hat before turning smartly on his heels and starting towards one of the customers.

Leonard bolted from his sunny window spot when he realized exactly who the devil was beelining towards. In a flash, Leonard had grabbed the devil by the arm and pulled him to a stop.

“I don’t know what business you think you have with that man, but he is under my protection.” Leonard’s voice was gruff, trying to intimidate the devil into leaving. Instead, he just smiled, giving the angel a proper once over.

“My apologies, Guardian. I sensed another otherworldly presence but I would not have thought you were an angel from your look.”

The devil did have a point. Leonard’s outfit choice of dark wash jeans, solid dark color t-shirts, and a black leather jacket was not the typical choice of those in his line of work. Actually, most of them preferred something more akin to what the devil was wearing. Something about being light and professional; Leonard just cared about being comfortable.

“Regardless, your business is done here,” he pulled the devil towards the door, “And you’d do yourself a favor to learn the auras of us celestials. Could save your ass one of these days.”

The devil laughed, “Oh, you even swear! Surprising. I thought you all were too stuck up and prudish for that.” He smirked, quirking his eyebrow in challenge. This devil was certainly something that Leonard had never come across before. He was almost… charming. If it wasn’t for the whole damned infernal thing, Leonard may even be hitting on him.

Regardless of any attraction, Leonard simply crossed his arms again, staring down the devil. He just smiled, hands in his pockets while he rocked back and forth on his feet. They stayed like this, caught in a stand-off, for a few minutes. The humans around them were oblivious, going about their daily routine as if two otherworldly beings weren’t trying to see who would break first.

The tension was only broken when Leonard heard Chris shut off his laptop and begin packing up to leave. The devil seemed to notice as well, as he held his hands up in defeat.

“You win this time, Angel. But I feeling our paths will cross again.”

With a bright smile and a wink, the devil vanished in a puff of red smoke that smelled of sulfur.

-

Sure enough, their paths crossed many more times. The devil was in a dogged pursuit of Chris, but Leonard always stepped in before contact could be made. They always exchanged some sort of witty banter, like two lions prowling around a meal. Leonard always won, but he often thought that he was just delaying the fight for another day.

This instance in particular was at Big Belly Burger. Chris was eating lunch with a friend, the first time in a few weeks that he’d been out and social. Leonard was happy that he was getting out of his apartment to see a friend, even if it was just at a fast food joint. A figure in white appearing outside the window caught his attention. At Leonard’s glare and narrowed eyes, the devil just gave him a big grin and waved. In a flash, Leonard was outside, almost nose to nose with him.

“He’s with a friend. He’s doing good. Leave him alone.”

Cocking his head, the devil responded, “Maybe I’m just here to see you. Ever consider that?” When Leonard didn’t respond, he just continued, “I do love our volleys of banter. I don’t have many conversations anymore that are with someone with a head on their shoulders.”

“Glad to hear I’m good company at the very least.” And perhaps knowing that the devil wanted to just be around him triggered something in Leonard. If heart fluttered a bit at the thought, well, he would never admit it.

“I’d like to know the name of my conversational partner,” The devil took a step back, handing over the power of the conversation to Leonard, “We’ve talked enough times that this feels almost a bit embarrassing to ask.”

He chuckled as he slid his hands into his pants pockets, a relaxed posed but a keen look in his eyes. He seemed honest enough, as honest as a devil could seem. Humans believe that names hold power and, well, they’re not _wrong_ per say. But between angels and demons, it gives neither of them power over the other. There was nothing holding him back, despite the excuse that Leonard scrambled to find.

After several beats of silence, realizing the angel wasn’t going to speak, the devil held out his hand, “Hello there Guardian. My name is Barry.”

Leonard cocked an eyebrow at that, “Really? Not Malphas or Valefar or something equally weird and old?”

“Well, it’s short for Bartholomew, but I’ve never gone by that,” he shrugged, chuckling a bit as he did, hand still extended, “Unless I was in trouble.”

For the first time in their interactions, Leonard let out a laugh. He shook Barry’s hand as he responded, “My name is Leonard.”

-

Barry hadn’t expected to feel such a… _something_ with this Guardian Angel. In fact, Barry had been determined to hate him, even if he’d never let the Angel know that. He’d been determined at first to get a deal with his human, but the Angel was equally determined to prevent it. It had been irritating at first, but after a few meetings Barry started to find it endearing. It was more than just that he was doing things by the book; the Angel seemed to genuinely care about his human.

Some humans didn’t have a Guardian Angel, regardless of their beliefs that everyone got one. It was mostly just the people who were in a bad patch. Anyone in that type of situation was a prime target for a devil to make a deal with, even if the person didn’t go out of their way to make the deal themself. The urgency to give themselves a better life cinched the deal for most people. Barry often didn’t even have to do much convincing. A lot of repeating of what he’s already said, but nothing more beyond that.

But this Guardian Angel was certainly giving him a hell of time. After several attempts, Barry started to question how much of his visits to this human were to attempt to make a deal and how much was to see this Angel. He certainly didn’t look like most angels, what with his dark clothes and brusque manners. But there was something about his dedication and steadfastness that enraptured Barry.

So, he started visiting him, always under the guise of trying to make a deal with the human. After a few visits, Barry realized that the Angel was always on guard while he was around: stiff posture, clenched jaw, stern eyes. He wasn’t relaxed.

In an attempt to relieve this, Barry properly introduced himself. He was being completely honest with reasons; Barry did truely want to know the Angel’s name. After all, it was only polite to call him by his name and not just refer to him as Angel or Guardian all the time.

He hadn’t been expecting ‘Leonard’. Something grander, probably Latin, something that would be positively stuffy and unbearable. But, granted that Leonard wasn’t your run-of-the-mill angel, it was only fitting he had a different name.

Barry was sure it was to become his favorite as his traitorous heart fluttered wildly as he left.

-

“You know,” Barry said as he stared up at the night sky, “I was human once.”

The two were sitting on top of Chris’s apartment building. Barry has no intention of making a deal with Chris anymore, regardless of what his boss told him. He’d shown up simply to hang out with Leonard. They’d hung out a few times since they exchanged names: at the post office while Chris worked, at the coffee shop where they first met, and a few times in the park nearby where Chris had started jogging.

It was in the park that Barry had first called him Len and, well, he hadn’t exactly stopped him. Just simply responded by calling Barry “Bear” or sometimes “Scarlet” due to his suit. Their hearts equally ached, unbeknownst to the other.

Maybe that’s why Barry was being so open now with Leonard.

“Human? That rarely happens. What was the special case?” You almost never heard of a human becoming a devil or an angel. When it did, the person was often one of two extremes. Len wondered what Barry had done to be made a devil.

“My mother…” Barry’s voice may have been steady, but Len could hear a slight edge to it. Had he been looking at him, he’d see the red flash in his eyes.

“She was killed. Someone broke into our house and killed her. When the cops showed up they blamed my dad. Saying he had to have done it. He was innocent. I tried talking to the police about it, but they weren’t going to listen to a kid.”

He dropped his head, shaking it, “I tried for _years_ to come up with evidence to exonerate him. I started working in forensics. But even after all that time… I couldn’t help him. So I took matters into my own hands.”

Realization washed over Leonard, “You made a deal.”

Nodding, Barry continued, “Crossroads demon. Gave him my soul for my father’s freedom. I thought my soul would go to him when I died-”

“But he claimed payment then.”

He exhaled a quiet ‘yeah’ as he kicked his feet out. Leonard looked at this… kid. All he had wanted to do was help his family, but he has his life and soul stolen from him.

He felt anger boil up in his chest, clawing at his stomach like a hunger he hadn’t felt in a millennia.

“My dad has been alone for over five years. He was devastated to find out his son - his only remaining family - had been killed in a hit and run shortly before his release. He couldn’t hold down a job for long. I haven’t interact with him - I don’t want to know what would happen to him if he saw me like this - but I’ve watched over him.”

Len nodded. He’d seen his fair share of awfulness in humans, the struggles they face even when trying to just be good.

“There was a girl,” he started, voice soft, “She was one of my first humans. Her name was Lisa.”

Memories flashed through his mind as he recounted the story from centuries earlier.

“She was quick-witted, cared for her friends. Her mother died giving birth to her, and I think that’s what did it for her father.”

Now it was Leonard’s turn to look out at the cityscape. What had once been an expanse of land untouched by humans was now nearly desolate of any signs of nature. Gray concrete and glass buildings reflecting nothing but more glass and concrete. At least everything was cleaner in a sense. Nothing like the soot covered slums Lisa had been in.

Len told of how he barely managed to breath life into her as her mother’s light faded. The father sat in the other room, anxiously waiting to hear the news. When the midwife informed him he had daughter, he was content, but at the news of his wife’s passing he was completely crushed.

“It was not a good start to their relationship,” Len recounted, “He always held some bitterness in his heart and over the years it festered and grew. He would hit her, get rough with her, and it always got worse when he drank. Which was often.”

“What happened to her?” Barry’s voice was soft. This was something that happened long before his time, and something so unfortunately common that wasn’t even an event of note to anyone aside from Leonard.

“Her father almost beat her death one night. She was laying on the floor, bloody and broken. I wasn’t going to let her die,” The event played over in Len’s head, flickering like film, and he took a deep, steadying breath before he continued, “I showed myself to them.”

There was a sharp intake of breath as the words registered in Barry’s mind. It was more common for demons and devils to show themselves to humans, often to make deals or in attempts to lead them astray. Angels on the other hand… well, they weren’t supposed to directly interact with humans. They were supposed to be more of a guiding force than a direct one. Unless given explicit orders from way up on high, an angel was never to show themselves.

“I had summoned myself as a light, bright and holy, hoping that maybe divine intervention would get the man to stop. He did, but out of fear. As he began praying, having fallen to knees, I told him he had no second chance and he would left alone, with neither wife nor daughter. And with a glowing hand, I picked up the girl, healing her, and took her to a better place.”

Leonard took the girl to a couple who had been trying desperately for children, but couldn’t have any. In the night, as they cried, Len knocked on their door, in a human form and with a cloak pulled over him and Lisa’s hand in his. The husband answered, and Len explained that he could not take care of this girl, who he claimed his sister, anymore. He knew of the couple’s struggles and entrusted her in their care. He did not know if the parents were just desperate, or if they sensed something about him, in his too blue eyes, but they took her in.

“They never hit her. They gave her a life that horrid man never would have. She grew up strong, but eventually fell to influenza. Not even I could have prevented that.”

Finally, Leonard turned to look at Barry, his eyes pricking with the threat of tears but he pushed them back. Barry’s expression was soft, understanding.

“I was there when she died. In her final moments, she saw me again. She recognized me and, with her final words,” He choked at the memory, “She thanked me.”

The memory was enough for Leonard to withstand the punishment he faced. He essentially got put in the divine equivalent of an office job for a few hundred years. Sorting through prayers and judgements and demon deals. It had all been worth it for that one life.

“That’s why you’re so protective of Chris.”

Len nodded and Barry finally, fully understood. Leonard may seem like a cold, snarky hard ass, but it’s only because he’s trying to protect those he cares about. And he really does care about his humans. It wasn’t just an act.

Reaching out, Barry placed his hand on top of Leonard’s, “Because I got crossed on my deal, I make sure to make the deals heavily in the human’s favor. I don’t reap souls unless absolutely need. I don’t hand out automatic wealth or happiness though; I just make it a bit easier for them.”

Not moving his hand, Len asked, “Why are you bringing this up?”

“I think maybe you should hear out my proposal for Chris.”

-

Between their meetings, Leonard pull up all of Bartholomew’s deals. Sure enough, they were almost entirely in the human’s favor. Seeing the evidence, he was reassured with what they were going to do.

-

It was a sunny day at the coffee shop. Chris was trying to relax, trying to come to terms with the fact he’d probably be stuck working at the post office for the rest of his life. Yeah, he worked long hours, and had basically no social life, but at least he made money.

He glanced over at the door when the bell jingled. Two men had walked in, one dressed in dark jeans and a t-shirt underneath a leather jacket. The other, peculiarly, was wearing a white and red suit. Chris didn’t noticed that no one else noticed the two. In fact, he was oblivious to the fact that no one else was moving. He did noticed that the two men - _“They must be couple”_ he thought to himself - approached his table in the corner.

The older looking one - the one with the leather jacket and almost unsettlingly blue eyes - pulled over a third chair and sat down. The younger one - clean shaven with a mischievous look in his eyes -  sat down in the other chair. Chris was frozen, unsure of what to do.

The two shared a glance before the older one spoke.

“Hello Chris.”

“H-how do you know my name?”

“I’ve been watching you for quite some time. As has my associate here, but I’ve been with you for far longer.”

He glanced back and forth between them. Surely these two were just some druggies hopped up on... _something_. As if reading his mind, the younger one laughed.

“We’re not druggies. Just an angel and a devil, here to make a deal.”

Chris almost didn’t believe them. But suddenly he noticed the spoon in mid fall a few tables over, the steam from a hot, fresh cup of tea frozen in air over on the counter, the way the two felt familiar but also incredibly powerful.

He decided to hear them out. They laughed as he guessed the older one was the devil and the younger the angel. They introduced themselves and laid out the deal. Chris wouldn’t owe them his soul or even undying patronage. He wouldn’t have to give his first born child or go off and join the military. Not even something weird like join a BDSM sex cult and get weird tattoos of various ruins. Nothing of the sort.

“The climb won’t be easy, but within the decade you’ll reach a point where you’ll be happy. You’ll have a job that doesn’t practically break your back, and you won’t have to worry about paying rent by compromising on food,” Barry explain, pointing to various clauses on the papers he had summoned and laid out on the table.

“What’s the catch?” Chris asked warily.

Len spoke up this time, “Be patient and be kind. Never hit another out of anger unless defending yourself in a fight or protecting the innocent. When you have extra money lining your pocket, consider giving it to the less fortunate or donating it to charity. Remember what it’s like to be in your seat now, and always remember that there are some who have it far worse than you currently.”

He didn’t believe it at first, but even as he read the contract word for word, he found that they were telling the truth. No room for double meanings or double crossing. It was as straightforward as they said.

With a shaky hand, he picked up the mahogany pen.

-

A decade later, Chris returned to the coffee shop. He hadn’t been there much in recent years, often travelling for his job. His memory of that day is foggy at best, but he feels strong ties to this date and this place. He places a kiss on his wife’s temple and tell her to go grab a table; he’ll place their orders and be over in a few moments.

They started dating five years ago and had been married for a year and a half. He smiled as he played with his wedding band. They’d met at a conference he attended for his job. Chris had long ago quit the post office and was now a historian at the Central City Historical Museum. The two had bonded over drinks one night, talking about the conference. When another attendee tried to grope her, Chris had stepped in, reprimanding the man and eventually getting him kicked out of the hotel bar. His wife had never forgotten it.

These had been the happiest years of his life. Never would he have thought that he’d get out of that slump he’d been in. But here he was.

A few minutes later, he sat down at the table, sliding a latte over to his wife. She smiled, thanked him and took a sip, proceeding to talk about a current work project. As she talked, the bell at the door jingled, and something in the back of Chris’s mind went off, causing him to look over. Approaching the barista was a couple: a man in a leather jacket and dark wash jeans holding hands with another man in a scarlet button up shirt and black skinny fit dress pants.

Something was familiar about them, but he couldn’t quite place it. The older man turned, and made eye contact with Chris. As he met those blue eyes, a brief flash of memories were triggered in Chris’s mind.

The two shared a soft smile as Chris realized who they were. With a brief nod of his head, he mouthed to the man ‘thank you’. Leonard just smiled, happy, before turning to place a kiss on Barry’s cheek.

“We’ve done well Scarlet. We’ve done well.”

**Author's Note:**

> Hope you guys enjoyed, regardless of character accuracy.
> 
> Check out my tumblr (thenameisz.tumblr.com) or some of the other stories I've written on here! Also, if you are strictly ColdFlash, go check out my friend's work!


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